Azo-dyestuffs and process of making same



Patented Sept. 5, 1933 UNITED STATES PATENT oFFxcE AZO-DYESTUFFS AND PROCESS OF MAKING;

SAME

Gerald Bonhote, Basel, Switzerland, assignor to Society of Chemical Industry in Basle, BaseL,

Switzerland No Drawing. Application March 25, 1933, Serial 7 N0.662-,8'34, and in Switzerland April 11(1932 16 Claims.

This invention relates to the manufacture of valuable new dyestuffs'by coupling anarylide of 2:3-hydroxynaphthoic acid of the general formula Y s arr- OH in which R1 stands for a nucleus oithe benzene or naphthaleneseries, with a diazo-cornpound obtained by diazotizing an. arylether of the general formula .in. which R2 stands for a nucleus oft-he benzene series. The dyestuffs thus obtained correspond to the general formula a;

r i H 6 OH O-Alkyl 0 R1. H A V or naphthalene series and B? for a nucleus of the benzene series. Thesedyestufis form in a dry state dark powders; and dissolve in pyridine to violet solutions. When produced on cotton,

in which B stands for nucleus of the; benzene they dye this fibre violet to blue-violet tints of (omen-95 The following examples illustrate the invention, the parts being by weight unless otherwise stated:-

Example 1 27.2 parts of 2-aminoe l-methoxy-d-acetylamino.-1:I'-diphenylether are diazotizedin the usual manner. The cleard-iazo-solution thus. ob.- tained is introduced; into a Solution; consisting of Parts of ZZBrhydIT XY JDh ac d- 9. 4. 7 anisidide, parts, of sodium hydroxide solution of 30. per cent. strength, 15, parts of anhydrous sodium carbonate and 2000; parts out water.. The dyestuffthus, formed, whichcorresponds very probably to the formula immediately separates. Its violet precipitate is filtered and dried. e

A Emme Cottonyarii is; impregnated; with a, grounding liquor made by. diSSOlVi'IlE-VG kilos, 0t 2 :3-.hydroxynaphthoic acid-2emethyl-emethoxy-anilide. in

300' cc. orhot water wi d i ionof- 1 2, c. of sodiumhydroxide solution; f 3Q-per cent, strength and 8 cc. of Turkey red oil, and then. diluting the .whole to 1 litre lhfi yarnis;v then wrung; out' oped. ina neutrali dsQL t Qn n ainamino=2,"-methyl,-.1;' :.ziph enylether; Therel f is produced a pure; violet of-. very goodv fastness, in: particular; ofexcellent. f-astness: to, light.v The tint of very good fastness.

formula of the new dyestuff corresponds probably to the formula very Similar violet tints are obtained with the 2:4-

dimethoxy-5-chloranilide of 2:3-hydroXynaph-- thoic acid. Blue-violet tints are obtained with the para-anisidide of 2:3-hydroxynaphthoic acid.

Example 3 Similar violet tints are obtained with the paraanisidide of 2:3-hydroxynaphthoic acid.

Example 4' 1 part of cotton mill is impregnated with 25 parts of a solution of '7' grams of 2:3-hydroxynaphthoic acid-orthoanisidide,"14cc. of a caustic soda solution of 30 per cent. strength, 10cc. of Turkey red oil and 7 cc. of formaldehyde solution of {i0 per cent. strength per litre, at 25-30 C. It is well wrung out and then developed in a a neutralized solution containing 3 grams of diazotized2-aminol-methoxy-5-acetylamino4'- methyl-1:1-diphenylether per litre. Rinsing and soaping follow. There is obtained a bluish-violet Violet tints are obtained with 2-methyl-4-methoxy-anilide of 2:3- hydroxynaphthoic acid. The formula of the new dyestuif corresponds very probably to the formula 7 Similar violet tints of like excellent properties are obtained with diazotized 2-amino-4-methoxy- 5-acetylamino-2 -ch1oro- 1 1 -diphenylether and the c-naphthalide or the u-naphthalide or'the 2 l-dimethoxy-5-chloranilide of 2 3-hydroxynaphthoic'acid, or if the 2-amino-4-methoxy-5- 1 acetylamino-Z chloro-l l -diphenylether is replaced by the 2-amino-4-ethoxy-5-acetylamino- 2 -chloro 1 1 -diphenylether.

Similar results are obtained in piece-dyeing or in printing. The dyestuffs may also be produced on other fibres, such as wool, silk or artificial silk, in which case, obviously, the mode of operation described in the preceding examples must correspondingly be altered as prescribed in the relevant literature (for instance patent application Serial No. 356,620)

What I claim is:-

1. A process for the manufacture of new azodyestuffs, consisting in coupling an arylide of 2 3-hydroxynaphthoic acid of the general formula in which R1 stands for a nucleus of the benzene or naphthalene series, with a diazo-compound obtained by diazotizing an arylether of the general formula O-Rg |-(l)-CHa H t I Alkyl in which R2 stands for a nucleus of the benzene series.

2. A process for the manufacture of new azodyestuffs, consisting in coupling an arylide of 2 3-hydroxynaphthoic acid of the general formula H I o H in which R1 stands for a nucleus of the benzene or naphthalene series, with a diazo-compound ob tained by diazotizing an arylether of the general formula in which R2 stands for a nucleus of the benzene series.

"tizing anarylether of theformula 13525342: 3. A process for the manufacture of newazodyestufis, consisting in coupling an arylide ofv 2 3-hydroxynaphthoic acid of the general formula series, with a diazo-compound obtained by diazotizing an arylether of the general formula in which R2 stands for a nucleus of the benzene series.

- 4. A process for the manufacture of new azo dyestuffs, consisting in coupling an arylideuof 2 3-hydroxynaphthoicacid of the general formula in which R1 stands for a nucleus of the benzene series, with a diazo-compound obtained by diazotizing an arylether of the general iormula HNGIFWP H 0 g CHa I in which R2 stands/for a nucleus of the benzene in which R1 stands for a nucleus of the benzene series, with a 'diazo-compound obtained by'diazo- O-CHs 6. A process for the manufacture of new azodyestuffs, consisting in coupling an arylide of 2:3-

hydroxynaphthoic acid of the general formula pound obtained bydia'zotizing an arylether .of the formula .7 V

, O-CH: 7. A process for the manufacture of a new azo- B5 dyestufi, consisting in coupling an arylide of 2:3- hydroxynaphthoic acid of the forx nulav Y o it with a diazo-compound obtained by diazotizing an-arylether of the formula (FOO-CH3 N-o c n 1V9 I H 0 0,0H3 8Q A process for the manufacture of a new azodyestufi, consisting in coupling an arylide of 2:3- P1P. hydroxynaphthoic acid of the formula 0 l "1139 with a .diaz'o-compound obtained by diazotizing an ,a'rylether ,ofthe formula HQN I] Ifi-CH5 H 0 04011, 1130 9. The azo-dyestuifs of the general formula I O-Rn it in which R1 stands for a nucleus of the benzene or naphthalene series, and Rz-for a vnucleus'of the benzene-series, which dyestuffs in a drytstaite. form dark powders, dissolve in pyridine to violet solutions, and, when produced on cotton, dye this fibre violet to blue-violet tints of excellent fastness, particularly to light, chlorine and kier-boiling.

10. The azo-dyestuifs of the general formua N: E-ECH3 OH CH: 1

ON-H

, M, p in which R1 stands for a nucleus of the benzene or naphthalene series, and R2 for a nucleus of the 159 benzene series, which dyestuffs in a dry state form dark powders, dissolve in pyridine to violet solutions, and, when produced on cotton, dye this fibre violet to blue-violet tints of excellent fastness, particularly to light, chlorine and ,kierboiling.

11. The azo-dyestufis of the general formula in which R1 stands for a nucleus of the benzene series and R2 for a nucleus of the benzene series, which dyestuffs in a dry state 'form dark powders, dissolve in pyridine to violet solutions, and, when produced on cotton, dye this fibre violet to blueviolet tints of excellent fastness, particularly to light, chlorine and kier-boiling.

12. The azo-dyestufis of the general formula in which R1 stands -for a nucleus of the benzene series, which dyestuifs in a dry state form dark powders, dissolve in pyridine to violet solutions, and, when produced on cotton, dye this fibre violet to blue-violet tints of excellent fastness, particularly to light, chlorine and kier-boiling.

13. The azo-dyestufisof the general formula in which R1 stands for a nucleus of the benzene series, which dyestufis in'a dryv state form dark powders, dissolve in pyridine to violet solutions, and, when produced 'on cotton, dye this fibre violet to blue-violet tints of excellent fastness,

- particularly to light, chlorineand kier-boiling.

14. The azo-dyestufis of the general formula ((-O-O-CH:

=N E-o-on;

I OH

--GHa ffo in which as stands for a substituent of a group consisting of H, CH3 orO-CI-Ia, which dyestuffs in a dry state form dark powders, dissolve in pyridine to violet solutions, and, when produced on cotton, dye this fibre violet to blue-violet tints of excellent fastness, particularly to light, chlorine and kier-boiling.

15. The azo-dyestuff of the formula N=N III-Cf-OH:

(L H OH CHa y) it which dyestuff forms ina dry state a dark powder, dissolves in pyridine to a violet solution, and, when produced on cotton, dyes this fibre violet tints of excellent fastness, particularly to light, chlorine and kier-boiling.

16. The azo-dyestuif of the formula which dyestui'f forms in a dry state a dark powder, dissolves in pyridine to a violet solution, and, when produced on cotton, dyes this fibre blueviolet tints of excellent fastness, particularly to light, chlorine and kier-boiling.

GERALD BONI-IOTE. 

